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The Tranny Affair  

PuffDaddy_2000 48M
380 posts
2/24/2015 5:31 am
The Tranny Affair

A flashback from the days of my youth...





Now, the thing about having sex with a woman with a cock is the mystery. There's a certain sinful foreboding about it because, ironically, one sees her a woman, not a man. The urge is riveting; the prospect, gripping; the release, otherworldly...

Back in 2002, I visited Bangkok (excuse the pun) for business; turns out I didn't bargain on pleasure! I'd heard about the ladyboys Thailand was famous for, but never gave it much thought. I was there for the sex and games, a bit of chemical abuse... you know how single boys in their late 20s do. So, I roll up with my boy Timo, who sells suits (I was thinking of going into business with him at the time, plus I needed a holiday from my career). First night in Bangkok was easy – clubbing, hooking up with a few cuties Timo knows, back to the hotel.

But the second night, he takes it a notch up.

“Ever had a Tranny?" He asks me.



By then, I hadn't embraced my sexuality, so the question's a bit dicey. At this point it would be nice to know that ALL guys want to have sex with a tranny. At least it's not as gay as having sex with a guy. Me, I'm a complete top. So I'll be doing all the doing. Anyway, we go a seedy part of town called Patpong — which just happens to be the red light district —and make a bar he knows.

The first thing I notice is the HOT women. Thai shemales are like no other people in the world. They are even quite different from other Thais. For a start, most Thai women are quite short, with flat asses, small tits and quashes, bulbous noses. But the average Thai shemale is actually taller than the average Thai man...



The first thing you notice are the tits: proud, jutting breasts with ever-erect inch-long nipples just crying out to be chewed. Next comes the ass, with firm, smooth coffee-colored buttocks poking out, challenging you: are you man enough to stick your cock here? The sensual, exotic face with those pouting lips and all-knowing eyes take your breath away. They can see right through you to your innermost desires, while their soft lips and probing tongue makes them come true. Taken separately, these features are impressive enough. But packaged together, they are almost too good to be true.

Anyway, we sit at the bar, get our drinks, and sooner or later, we have company. More drinks and laughter, and the inhibitions start creeping away. By this point, I KNOW she's a ladyboy, but she hasn't told me yet. Timo moves with his date to the lounge side of the bar, and I start getting comfortable with mine. Then comes the kissing, deep French kissing, and she whispers in my ear (while now stroking and intermittently grabbing my cock), "You look like a big boy. I think I have a surprise for you!"



This goes on for a bit, and eventually it's time to get back to the hotel. There's no doubt in anyone's mind that we're going to fuck. Well, we get to the hotel (the taxi being those van types, so each one of us seated with our dates - snogging, sucking tits etc.). Well, we get to our hotel, head straight to my room, lock it, and start necking the girl. Things get real hot, and I'm wondering when the (her) hard-on will start showing. But it doesn't. Now she's pretty much naked, except for a thong and a Wonderbra, and the body is gorgeous! We manoeuvre to have her on top of me. She's now kissing my mouth, deeply and with intent; sucking on my nipples, rubbing my cock. Then she removes my trousers and starts sucking my cock. There's something about one's cock being sucked by another man, and It completely blows (excuse the pun) my mind; the best blowjob I've had by a mile. I blow my load in her mouth, and she swallows.

Then she announces that it's time for a "surplise", turns around (ass facing me now - the most curvaceous and tightest, most shapely ass ever) and starts a strip tease. Out goes the bra, and she turns around to show me the boobies, then turns back, bends over and slides off the thong. I am riveted to the bed, horny as a fool. Then she asks me if I like her "surplise". She moves slowly towards me, lying supine in bed, naked. She goes straight for the cock, and another mind-boggling blowjob ensues. At some point I'm taken over, and suck her cock, which is even bigger than mine!



The blowjob goes on for a bit, partly due to her skill and the fact that I love my cock sucked, so I stop her every time I want to cum, rest for a bit, and continue. Eventually, I put on a rubber, turn her on her tummy and ram her from behind, on top of her. I come in exactly 6 minutes. But she's not heard the last from me. I have a quick sluice, pour some drinks, and we chat in broken English for a bit. Then it's time to continue. The door to sin has been opened, and there's no turning back now...

longlustlover66 43M
29 posts
8/17/2016 12:01 pm

Nice. So begins the slippery slope of fandom. Never going to put that back in the closet.


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